Gaseous Hydrogen Reactant Patents (Class 568/462)
  • Patent number: 10189766
    Abstract: A process for producing 2-ethylhexanal involves performing reaction using a reaction tank equipped with a gas-introducing mixer having extracting, exhausting, and stirring functions in the presence of a palladium on carbon catalyst having a carbon carrier with lower impurity content and higher specific surface area for hydrogenation, and introducing hydrogen gas evenly into reaction liquid; resulted in that the process minimizes operational pressure for hydrogenation and increases a yield of 2-ethylhexanal at least up to 98.0%.
    Type: Grant
    Filed: August 28, 2017
    Date of Patent: January 29, 2019
    Assignee: NAN YA PLASTICS CORPORATION
    Inventors: Te-Chao Liao, Jung-Jen Chuang, Chung-Yu Chen, Chia-Ruey Tsai, Sung-Chieh Chao
  • Patent number: 8692028
    Abstract: Disclosed is a method of hydrogenating an 1,2-unsaturated carbonylic compound to obtain the corresponding saturated carbonylic compound in the presence of a palladium catalyst with heterogeneous distribution of palladium.
    Type: Grant
    Filed: December 21, 2010
    Date of Patent: April 8, 2014
    Assignee: BioFuel-Solution i Malmo AB
    Inventors: Christian Hulteberg, Jan Brandin
  • Patent number: 8389775
    Abstract: The invention relates to a process for preparing polyether alcohols, which comprises the steps a) reaction of an unsaturated natural oil or fat with a mixture of carbon monoxide and hydrogen, b) reaction of the mixture from step a) with hydrogen, c) reaction of the product from step b) with an alkylene oxide in the presence of a catalyst.
    Type: Grant
    Filed: January 26, 2009
    Date of Patent: March 5, 2013
    Assignee: BASF SE
    Inventors: Darijo Mijolovic, Andrea Haunert, Andreas Kunst, Stephan Bauer, Qiang Miao, Berend Eling
  • Publication number: 20120323043
    Abstract: Disclosed is a method of hydrogenating an 1,2-unsaturated carbonylic compound to obtain the corresponding saturated carbonylic compound in the presence of a palladium catalyst with heterogeneous distribution of palladium.
    Type: Application
    Filed: December 21, 2010
    Publication date: December 20, 2012
    Applicant: BioFuel-Solution i Malmo AB
    Inventors: Christian Hulteberg, Jan Brandin
  • Publication number: 20080081931
    Abstract: Disclosed are processes for the preparation of glycolaldehyde in which formaldehyde is contacted with carbon monoxide and hydrogen in the presence of a rhodium catalyst and a solvent containing at least one N,N-dihexylbutyramide. The glycolaldehyde product is recovered by extraction with water. The process provides high selectivity to glycolaldehyde and efficient separation of hydroformylation products from the solvent and rhodium catalyst.
    Type: Application
    Filed: September 12, 2007
    Publication date: April 3, 2008
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Thomas Allen Puckette, Thomas James Devon
  • Publication number: 20070282135
    Abstract: Process for the catalytic hydrogenation of methylolalkanals of the general formula where R1 and R2 are each, independently of one another, a further methylol group or an alkyl group having from 1 to 22 carbon atoms or an aryl or aralkyl group having from 6 to 33 carbon atoms, in the liquid phase by means of hydrogen over a hydrogenation catalyst, wherein hydrogen is used in a molar ratio to methylolalkanal of greater than 1.
    Type: Application
    Filed: June 6, 2006
    Publication date: December 6, 2007
    Applicant: BASF Aktiengesellschaft
    Inventors: Steffen Maas, Thorsten Johann, Michael Koch, Tilman Sirch, Stephan Schlitter, Stefan Rittinger, Michael Steiniger, Todd C. Spengeman
  • Patent number: 7094932
    Abstract: The present invention provides a method for the production of glycolaldehyde with high specificity. The hydrous thermolysis consists of the spraying of aqueous sugar solutions containing from 25 to 80% of water but preferably 30 to 60% water, as a fine mist into a reactor held at the between 500 and 600° C., but preferably between 520 and 560° C. and the condensation of the resulting vaporous product in a surface condenser with optional heat recovery. The residence time of the vaporous product in the reactor should be in the range 0.1–5 seconds, but preferably in the range 0.5 to 2 seconds. Aldose monomeric sugars, preferably glucose (also known as dextrose), are preferred for use in the aqueous solution. The yield of glycolaldehyde in the condensed liquid is minimum 50% by weight of the sugar fed for glucose solutions.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: August 22, 2006
    Assignee: Resource Transforms International Ltd.
    Inventors: Piotr A. Majerski, Jan K. Piskorz, Desmond St. A. G. Radlein
  • Patent number: 6787677
    Abstract: In a process for the catalytic hydrogenation of a carbonyl compound or a mixture of two or more carbonyl compounds in the presence of catalyst tablets which comprise an inorganic, TiO2-containing support and, as active component, copper or a mixture of copper with at least one metal selected from the group consisting of zinc, aluminum, cerium, nobel metals and metals of transition group VIII and whose copper surface area is not more than 10 m2/g, the diameter d and/or the height h of the tablets is less than 3 mm.
    Type: Grant
    Filed: September 29, 2003
    Date of Patent: September 7, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Koch, Steffen Maas, Wolfgang Jürgen Pöpel, Matthias Dernbach
  • Patent number: 6369277
    Abstract: An &agr;,&bgr;-unsaturated carbonyl compound of formula (I) where R1 is saturated C1-40-hydrocarbyl or a substituted or unsubstituted aromatic radical containing moiety, and R2, R3 and R4, independently of one another, are hydrogen or a C1- to C4-alkyl group, is selectively hydrogenated in the liquid phase to a saturated carbonyl compound of formula (II) with hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base, by conducting the hydrogenation in a packed bubble column reactor in which product is recycled and hydrogen gas is recirculated.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: April 9, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Josef Broecker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Guenter Wegner, Manfred Stroezel
  • Patent number: 6340778
    Abstract: The invention relates to a process for the catalytic aldol condensation of aldehydes by means of a multiphase reaction in a tube reactor, wherein the catalyst is present in the continuous phase and at least one aldehyde is present in a dispersed phase and the loading factor B of the tube reactor is equal to or greater than 0.8; the aldol condensation products obtained in this way can be used for preparing alcohols or carboxylic acids.
    Type: Grant
    Filed: October 24, 2000
    Date of Patent: January 22, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann, Juergen Koch
  • Patent number: 6150564
    Abstract: The invention relates to a process for the selective liquid-phase hydrogenation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I, ##STR1## where R.sub.1 is hydrogen or an organic radical, and R.sub.2, R.sub.3 and R.sub.4, independently of one another, are hydrogen or a C.sub.1 -- to C.sub.4 --alkyl group, to saturated carbonyl compounds of the formula II ##STR2## using hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base. The process is carried out in a packed bubble column reactor (1, 2) with product recycling (11, 17) and circulating hydrogen gas (4, 15, 16). It is particularly suitable for the selective hydrogenation of citral to citronellal.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: November 21, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Josef Brocker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Gunter Wegner, Manfred Stroezel
  • Patent number: 6114588
    Abstract: A method to produce dialcohols is provided, the method comprising the steps of:providing a feed stream comprising an alpha-alcohol-diolefin;reacting the feed stream with hydrogen and carbon monoxide in the presence of a catalyst system comprising a cobalt phosphine ligand complex under conditions effective to hydroformylate at least a portion of the diolefin in the feed stream; andrecovering the dialcohol from the reacted feed stream. This method is a one-step process to hydroformylate alpha-alcohol-diolefins such as 2,7-octadien-1-ol to produce a significant yield of dialcohols such as 1,9-nonanediol.
    Type: Grant
    Filed: June 11, 1998
    Date of Patent: September 5, 2000
    Assignee: Shell Oil Company
    Inventors: Pui-Kwan Wong, Andrew Allison Moxey
  • Patent number: 5756856
    Abstract: The present invention relates to a process for the preparation of 2-ethylhexanal by catalytic hydrogenation of 2-ethylhex-2-enal, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding 2-ethylhex-2-enal and hydrogen to an upper part of a reactor to catalytically hydrogenate said 2-ethylhex-2-enal to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein 2-ethylhex-2-enal is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating step (c) until the subsequent reactor is the last reacto
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: May 26, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • Patent number: 5650546
    Abstract: A process for the hydrogenation of organic compounds using water soluble catalyst in a biphasic media by: (A) forming an organo-water dispersion of (i) an organic phase having (a) an organic compound and (b) an organic solvent, and (ii) an aqueous phase having a water soluble group VIII metal catalyst composition and a water soluble ligand; and (B) contacting said dispersion with hydrogen to provide an interfacial reaction between said organic compound and said hydrogen, giving significant enhancement in the rate of reaction to produce saturated organic compound as compared to a reaction carried out in the absence of said water immiscible ligand.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: July 22, 1997
    Assignee: Council of Scientific Industrial Resear.
    Inventors: Raghunath Vitthal Chaudhari, Bhalchandra Mahadeo Bhanage, Sunil Sadashiv Divekar, Raj Madhukar Deshpande
  • Patent number: 5254743
    Abstract: Solid solutions of a class of divalent metal oxides and a class of trivalent metal oxides resulting from calcination of layered double hydroxides related to hydrotalcite have been prepared with a surface area in excess of 150 m.sup.2 /g. Such high surface area materials are found to be quite effective in the aldol condensation of aldehydes and ketones, and in particular in the conversion of n-butyraldehyde to 2-ethyl-2-hexenal in high yield and with good selectivity in a liquid phase reaction at temperatures under about 200.degree. C. Variants can be devised where the aldol condensation product, an .alpha.,.beta.-unsaturated aldehyde or ketone, is concurrently reduced to the saturated alcohol under process conditions.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: October 19, 1993
    Assignee: UOP
    Inventors: Jennifer S. Holmgren, Blaise J. Arena
  • Patent number: 5235118
    Abstract: Disclosed is a continuous process for the manufacture of 2-ethyl-2-(hydroxymethyl)hexanal wherein 2-ethylhexanal, formaldehyde and a tertiary amine are continuously fed to a reaction zone and crude product comprising an aqueous phase and an organic phase containing 2-ethyl-2-(hydroxymethyl)hexanal and 2-ethylhexanal is continuously removed from the reaction zone Also disclosed are processes for (1) the azeotropic distillation of the organic phase of the crude product whereby unreacted 2-ethylhexanal is recovered and (2) the catalytic hydrogenation of the refined, organic phase of the crude product to produce 2-butyl-2-ethyl-1,3-propanediol.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: August 10, 1993
    Assignee: Eastman Kodak Company
    Inventors: Don L. Morris, William A. Beavers, William E. Choate
  • Patent number: 5026919
    Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: June 25, 1991
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 5015780
    Abstract: Dihalobutyraldehydes of formula I ##STR1## wherein X and Y are each independently of the other Cl or Br, are obtainable at high rates of conversion and with excellent selectivities by catalytic dehalogenation with hydrogen by carrying out the reaction with appropriate .alpha.,.alpha.-dihalobutyraldehydes in an organic aprotic solvent. The dihalobutyraldehydes are intermediates for the synthesis of herbicidal acyl cyclohexanediones.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: May 14, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Steiner, Hans Tobler
  • Patent number: 5003110
    Abstract: Saturated aldehydes are prepared by hydrogenation of .alpha.,.beta.-unsaturated aldehydes in a two-phase medium in the presence of a catalyst consisting of a rhodium derivative combined with a water-soluble ligand or of a rhodium complex with a water-soluble ligand.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: March 26, 1991
    Assignee: Rhone-Poulenc Sante
    Inventor: Jean-Michel Grosselin
  • Patent number: 4847423
    Abstract: Aqueous formaldehyde is hydroformylated to glycol aldehyde in the presence of a rhodium-phosphine ligand complex catalyst in which the phosphine ligand is a trialkyl- or tricycloalkylphosphine and has a specified cone angle. A preferred phosphine ligand is tricyclohexylphosphine.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: July 11, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Robert J. Koprowski, Jerry D. Unruh
  • Patent number: 4701562
    Abstract: Aldehydes can be condensed with ketones or aldehydes to produce higher aldehydes or ketones by contacting the materials to be condensed with a nonzeolitic molecular sieve. The condensation may be carried out in the presence of hydrogen to give as product a saturated aldehyde or ketone. The ketone and/or aldehyde may be generated in situ by dehydrogenation of an alcohol, and the hydrogen thus liberated used to effect hydrogenation of the immediate unsaturated product of the condensation, thereby producing as the final product a saturated aldehyde or ketone. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional catalysts for the reaction.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: October 20, 1987
    Assignee: Union Carbide Corporation
    Inventor: Kurt D. Olson
  • Patent number: 4677230
    Abstract: 2-Methyl-2-alkenals of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, alkyl which may additionally carry aromatic radicals, or an aromatic radical, are prepared by isomerizing a 2-alkylacrolein of the formula ##STR2## in the presence of hydrogen and of a catalyst which contains palladium and an oxide or salt of a rare earth metal as active components, at from 20.degree. to 120.degree. C. and under from 1 to 100 bar.
    Type: Grant
    Filed: June 11, 1986
    Date of Patent: June 30, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Leopold Hupfer, Franz Merger, Franz J. Broecker, Rolf Fischer
  • Patent number: 4608444
    Abstract: A process and accompanying catalyst for the hydroformylation of formaldehyde to glycol aldehyde is disclosed. The process features the utilization of (1) a class of transition metal phosphine-amide complexes, (2) a class of transition metal phosphine-amine complexes, and (3) mixtures of 1 and 2 as particularly suitable for use.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: August 26, 1986
    Assignee: The Halcon SD Group, Inc.
    Inventor: Stephen E. Jacobson
  • Patent number: 4605797
    Abstract: Selective hydrogenation process is provided employing as catalyst a composition consisting essentially of elemental palladium on calcium carbonate support with lead acetate and an aromatic amine oxide. Very high selectivities to cis-olefinic compounds from acetylenic compounds is achieved employing the catalyst of the invention.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: August 12, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4599469
    Abstract: Process for the hydrogenation of functionally substituted acetylenic compounds employing catalyst comprising nickel boride on an inorganic oxide support is disclosed. Functionally-substituted acetylenic compounds are selectively reduced under mild reaction conditions to give functionally-substituted cis-olefinic compounds in high yield.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: July 8, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Ted H. Cymbaluk, Jim D. Byers, Marvin M. Johnson
  • Patent number: 4590298
    Abstract: This invention provides a process for the production of C.sub.4 -C.sub.5 hydroxyketones by reaction of formaldehyde and synthesis gas in a basic organic solvent in the presence of a tungsten and Group VIII metal-containing catalyst composition.
    Type: Grant
    Filed: March 5, 1985
    Date of Patent: May 20, 1986
    Assignee: Celanese Corporation
    Inventor: Tessie M. Che
  • Patent number: 4560806
    Abstract: An improved transition metal-phosphine-amide hydroformylation catalyst is disclosed having a substantially increased solubility in non-polar organic solvents, thereby preventing migration of the catalyst into the glycol aldehyde product during the hydroformylation process and subsequent separation operations, greatly facilitating and improving the catalyst separation and recycle operations.
    Type: Grant
    Filed: April 5, 1984
    Date of Patent: December 24, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Stephen E. Jacobson
  • Patent number: 4503260
    Abstract: Hemi-formals are reacted with hydrogen and carbon monoxide in the presence of certain rhodium catalysts to form glycol aldehyde.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: March 5, 1985
    Assignee: Monsanto Company
    Inventors: Steven R. Auvil, Patrick L. Mills
  • Patent number: 4496781
    Abstract: A process for the preparation and purification of a glycol aldehyde intermediate which is later hydrogenated to ethylene glycol is disclosed. The process proceeds via the catalytic reaction of formaldehyde, carbon monoxide and hydrogen and utilizes a novel class of lipophilic rhodium phosphine amide catalysts and an effective solvent mixture, which enables efficient catalyst separation and recycle without the loss of a substantial amount of the expensive catalyst.
    Type: Grant
    Filed: April 5, 1984
    Date of Patent: January 29, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventors: Stephen E. Jacobson, Chun F. Chueh
  • Patent number: 4477685
    Abstract: Formaldehyde is reacted with hydrogen and carbon monoxide with rhodium catalyst in the presence of phosphine ligands having electron-withdrawing substituents, obtaining high selectivity to glycol aldehyde with a stable catalyst system.
    Type: Grant
    Filed: August 20, 1982
    Date of Patent: October 16, 1984
    Assignee: Monsanto Company
    Inventor: Albert S. Chan
  • Patent number: 4450300
    Abstract: For the continuous manufacture of n-butyraldehyde by selective hydrogenation of crotonaldehyde, the hydrogenation is conducted in the liquid phase in the presence of a palladium-aluminum oxide supported catalyst containing the palladium in the outer layer of the supporting grain of a thickness of 0.05-0.2 mm. The palladium content of this catalyst is 0.1-0.6% by weight. The aluminum oxide support, with a specific pore volume of 0.4-0.6 cm.sup.3 /g, has 40-60% of its pores of a diameter of >0.5 nm and an internal surface area of 130-160 m.sup.2 /g. The hydrogenation is conducted under absolute pressures of 5-50 bar and at temperatures of 20.degree.-100.degree. C. The resultant n-butyraldehyde is of a high purity without interfering by-products.
    Type: Grant
    Filed: March 12, 1982
    Date of Patent: May 22, 1984
    Assignee: Chemische Werke Huels Aktiengesellschaft
    Inventors: Lothar Fischer, Manfred Z. Hausen, Kurt Wember
  • Patent number: 4429165
    Abstract: Process for selective production of acetaldehyde and dimethyl acetal by the reaction of methanol with carbon monoxide in contact with a catalyst containing cobalt atom, halide atom and a mixture of a trivalent phosphorus compound and a trivalent nitrogen compound. The amount of trivalent nitrogen compound in its mixture varies from 5 mole percent to 50 mole percent of such mixture.
    Type: Grant
    Filed: June 24, 1982
    Date of Patent: January 31, 1984
    Assignee: Union Carbide Corporation
    Inventor: Richard W. Wegman
  • Patent number: 4420648
    Abstract: Supported coprecipitated cobalt-silica hydrogenation catalysts are disclosed. The catalysts are prepared by: preparing an aqueous reaction mixture containing cobalt cations, silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the cobalt and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the cobalt and silicate ions onto said solid porous carrier particles. The aqueous reaction mixture may additionally include copper cations.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: December 13, 1983
    Assignee: Exxon Research and Engineering Co.
    Inventors: James L. Carter, Allan E. Barnett
  • Patent number: 4414421
    Abstract: A process for the preparation of glycol aldehyde, which comprises reacting formaldehyde with hydrogen and carbon monoxide, in the presence of a rhodium- and/or a cobalt-containing catalyst, sulphur dioxide, and water.
    Type: Grant
    Filed: May 26, 1982
    Date of Patent: November 8, 1983
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4405821
    Abstract: In the process for producing glycolaldehyde and/or ethylene glycol by the reaction of formaldehyde, carbon monoxide and hydrogen in a non-amide solvent at elevated temperature and superatmospheric pressure in the presence of a catalytic amount of a rhodium-containing catalyst, an improvement is provided which comprises carrying out said reaction in the presence of a glycolaldehyde yield-enhancing phosphine oxide.
    Type: Grant
    Filed: August 11, 1981
    Date of Patent: September 20, 1983
    Assignee: National Distillers and Chemical Corporation
    Inventor: Richard W. Goetz
  • Patent number: 4405814
    Abstract: Formaldehyde is reacted with hydrogen and carbon monoxide in the presence of certain rhodium catalysts and basic organic amine compositions which promote the formation of glycol aldehyde.
    Type: Grant
    Filed: August 5, 1981
    Date of Patent: September 20, 1983
    Assignee: Monsanto Company
    Inventors: W. Eamon Carroll, Albert S. Chan
  • Patent number: 4394525
    Abstract: A process for hydrogenating an unsaturated organic compound which comprises contacting the same with hydrogen in the presence of a catalyst composed of a support containing (1) at least one Group IIA metal compound selected from the group consisting of magnesium, calcium, strontium and barium compounds, (2) alumina and (3) aluminum phosphate carrying nickel thereon.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: July 19, 1983
    Assignee: Gulf Research & Development Company
    Inventors: Roger F. Vogel, George Marcelin, Harold E. Swift
  • Patent number: 4382148
    Abstract: A process for the preparation of glycol aldehyde, which comprises reacting formaldehyde with hydrogen and carbon monoxide, in the presence of a catalyst system derived from a rhodium-containing catalyst precursor and/or a cobalt-containing catalyst precursor together with a strong protonic acid.
    Type: Grant
    Filed: October 27, 1981
    Date of Patent: May 3, 1983
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4365095
    Abstract: A process for hydrogenating an unsaturated organic compound which comprises contacting the same with hydrogen in the presence of a catalyst composed of a support containing (1) (A) a Group IIB metal compound selected from the group consisting of zinc and cadmium compounds, (B) a combination of said zinc and cadmium compounds or (C) a combination of at least one of said Group IIB metal compounds with at least one Group IIA metal compound selected from the group consisting of magnesium, calcium, strontium and barium compounds, (2) alumina and (3) aluminum phosphate and carrying nickel thereon.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: December 21, 1982
    Assignee: Gulf Research & Development Company
    Inventors: George Marcelin, Roger F. Vogel, Harold E. Swift
  • Patent number: 4361705
    Abstract: A process for hydrogenating an unsaturated organic compound which comprises contacting the same with hydrogen in the presence of a catalyst composed of a support containing alumina and aluminum phosphate carrying nickel thereon.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: November 30, 1982
    Assignee: Gulf Research & Development Company
    Inventors: George Marcelin, Roger F. Vogel, Harold E. Swift
  • Patent number: 4317945
    Abstract: A process for the preparation of 2-methyl-2-sec.butyl-1,3-propanediol comprising hydroformylating 2-methyl-1-butene with carbon monoxide and hydrogen in the presence of a first catalyst to form the substance 3-methyl-pentanal, condensing said substance with formaldehyde, or a compound which forms formaldehyde under the conditions of condensation in a basic medium to form alpha-sec.butyl-acrolein, partially hydrogenating said acrolein in the presence of a second catalyst to form the material 2,3-dimethyl pentanal, and converting said material into said diol by treatment with formaldehyde, or a compound which forms formaldehyde under the conditions of conversion, in the presence of a strong base as a third catalyst.The compound of the present invention is useful as an intermediate in the production of pharmaceuticals and drugs; in particular, the production of carbamates which are useful as tranquilizers and blood pressure lowering agents.
    Type: Grant
    Filed: August 15, 1980
    Date of Patent: March 2, 1982
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Wolfgang Bernhagen, Jurgen Weber, Helmut Bahrmann, Helmut Springer
  • Patent number: 4317925
    Abstract: A process for the preparation of di-n-propylacetic acid which comprises the steps ofA. converting n-valeraldehyde-diallyl acetal into allyl-1-pentenyl ether by cleaving one mol of allyl alcohol per one mol of n-valeraldehye-diallyl acetal;B. rearranging the allyl-1-pentenyl ether thermally into 2-propyl-pent-4-en-1-al,C. partially hydrogenating the 2-propyl-pent-en-1-al catalytically to form 2-propyl valeraldehyde, andD. oxidizing the 2-propyl valeraldehyde to form dipropyl-acetic acid.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: March 2, 1982
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
  • Patent number: 4291179
    Abstract: Acetaldehyde and ethanol are produced by the catalyzed reaction of formaldehyde, carbon monoxide and hydrogen using a halogen-containing rhodium catalyst.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: September 22, 1981
    Assignee: National Distillers and Chemical Corp.
    Inventors: Richard W. Goetz, Lawrence D. Meixsel, David W. Smith
  • Patent number: 4273945
    Abstract: Saturated aliphatic, cycloaliphatic and araliphatic aldehydes are prepared by selective hydrogenation of the corresponding olefinically unsaturated aldehydes with hydrogen in the liquid phase over a palladium-containing catalyst, using a catalyst system in which the active constituents are from 2 to 90% by weight of palladium and from 10 to 98% by weight of an oxide or a salt of a rare earth metal or of a mixture of different oxides and/or salts of this type.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: June 16, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Heilen, Axel Nissen, Wolfgang Koernig, Michael Horner, Werner Fliege, Guenter Boettger
  • Patent number: 4270006
    Abstract: Aliphatic carbonyl compounds are prepared by an aldol condensation of carbonyl compounds R.sup.1 --CH.sub.2 --CO--R.sup.2 (I; R.sup.1 and R.sup.2 =H or C.sub.1 -C.sub.8 -alkyl) in the presence of hydrogen and of a catalyst which has both condensing and hydrogenating properties, by using a catalyst system wherein the active components are from 1 to 90 percent by weight of a noble metal of group VIII of the periodic table and from 10 to 99 percent by weight of an oxide or salt of a rare earth metal, or of a mixture of different oxides and/or salts of rare earth metals.
    Type: Grant
    Filed: December 27, 1979
    Date of Patent: May 26, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Heilen, Axel Nissen, Otto Woerz
  • Patent number: 4267384
    Abstract: Acetaldehyde and ethanol are produced by the reaction of formaldehyde, carbon monoxide and hydrogen using a halogen-containing ruthenium catalyst.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: May 12, 1981
    Assignee: National Distillers and Chemical Corp.
    Inventor: David W. Smith
  • Patent number: 4263225
    Abstract: Supported coprecipitated nickel-cobalt-silica and nickel-cobalt-copper-silica hydrogenation catalysts are disclosed. The catalysts are prepared by preparing an aqueous reaction mixture containing nickel and cobalt cations (and optionally copper cations), silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the nickel, cobalt (and optionally copper) and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the nickel, cobalt (and optionally copper) and silicate anions onto said solid porous carrier particles.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: April 21, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: James L. Carter, Allan E. Barnett, John H. Sinfelt
  • Patent number: 4260829
    Abstract: Carbonyl compounds R.sup.1 --CHR.sup.2 --CHR.sup.3 --CR.sup.4 O (I, R.sup.1 =H or an organic radical; R.sup.2 -R.sup.4 =H or C.sub.1 -C.sub.4 -alkyl) are prepared by selective hydrogenation of the .alpha.,.beta.-unsaturated carbonyl compounds R.sup.1 --CR.sup.2 =CR.sup.3 --CR.sup.4 O (II) in the liquid phase by means of hydrogen in the presence of a palladium catalyst and of from 15 to 50% by weight, based on (II), of a tertiary amine.
    Type: Grant
    Filed: August 17, 1979
    Date of Patent: April 7, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Axel Nissen, Peter R. Laurer, Matthias Irgang, Heinrich Pasedach
  • Patent number: RE32084
    Abstract: A process for preparing glycol aldehyde by reacting formaldehyde, hydrogen and carbon monoxide at elevated temperature and superatmospheric pressure in the presence of rhodium catalyst and conversion thereof to ethylene glycol as the substantially exclusive polyol product.
    Type: Grant
    Filed: October 4, 1983
    Date of Patent: February 18, 1986
    Assignee: National Distillers and Chemical Corporation
    Inventor: Richard Goetz